N,N'-Di-Boc-N''-triflylguanidine | 286955-44-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N'-Di-Boc-N''-triflylguanidine
• 英文别名: tert-butyl [N-(tert-butoxycarbonyl)-N'-(trifluoroacetyl)carbamimidoyl]carbamate；tert-butyl N-[[(2-methylpropan-2-yl)oxycarbonylamino]-[(2,2,2-trifluoroacetyl)amino]methylidene]carbamate
• CAS: 286955-44-0
• 化学式: C₁₃H₂₀F₃N₃O₅
• 分子量: 355.314
• InChiKey: AMDNLZSDZZSQLS-UHFFFAOYSA-N

物化性质

• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N,N'-Di-Boc-N''-triflylguanidine 在 四丁基氟化铵 、 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 C₁₆H₂₉N₃O₅
  参考文献：
  名称：

  Total synthesis of (±)-martinelline

  摘要：

  The squaric acid-catalyzed imino-Diels-Alder reaction of enamine 4 with the imine 5 provides the pyrroloquinolines 6 and 7, which were converted to the triamine 3 using regioselective reduction and a Wittig reaction as the key steps. Guanylation of 3 followed by coupling with the alcohol 19 furnished the total synthesis of (+/-)-martinelline. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02331-6
• 作为产物：
  描述：

  三氟乙酸酐 、 1,3-二(叔丁氧基羰基)胍 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N,N'-Di-Boc-N''-triflylguanidine
  参考文献：
  名称：

  2H-phthalazin-1-one derivatives and drug containing its derivatives as active ingredient

  摘要：

  聚(ADP-核糖)聚合酶抑制剂，其活性成分为一般式(I)所代表的2H-邻苯二酮衍生物，或其盐。一般式(I)的化合物抑制聚(ADP-核糖)聚合酶，可用作各种缺血性疾病（脑部、心脏、消化道、骨骼肌、视网膜等）、炎症性疾病（炎症性肠道疾病、多发性硬化症、关节炎等）、神经退行性疾病（锥体外症、阿尔茨海默病、肌营养不良等）、糖尿病、休克、头部外伤、肾功能不全、过敏症等的预防和/或治疗药物。这些化合物还可用作逆转录病毒（HIV等）和癌症化疗药物的增敏剂。

  公开号：

  US06677333B1

文献信息

• Design, Synthesis, and Structure–Activity Relationship Studies of a Potent PACE4 Inhibitor
  作者：Anna Kwiatkowska、Frédéric Couture、Christine Levesque、Kévin Ly、Roxane Desjardins、Sophie Beauchemin、Adam Prahl、Bernard Lammek、Witold Neugebauer、Yves L. Dory、Robert Day

  DOI：10.1021/jm401457n

  日期：2014.1.9

  position with arginine mimetics were tested for their inhibitory activity, specificity, stability, and antiproliferative effect. By incorporating d isomers at the P8 position or a decarboxylated arginine mimetic, we obtained analogues with an improved stability profile and excellent antiproliferative properties. The DLeu or DNle residue also has improved specificity toward PACE4, whereas specificity was reduced

  PACE4在前列腺癌的进展中起重要作用，并且是开发新型基于抑制剂的肿瘤疗法的有吸引力的靶标。我们先前曾报道设计和合成一种新型，有效且相对选择性的PACE4抑制剂，称为Multi-Leu（ML）肽。在本工作中，我们通过详细的结构-活性关系研究检查了ML肽。测试了在P8–P5位置被亮氨酸异构体（Nle，DLeu和DNle）修饰或在P1位置被精氨酸模拟物取代的各种ML肽类似物的抑制活性，特异性，稳定性和抗增殖作用。通过合并d在P8位置的异构体或脱羧精氨酸模拟物，我们获得了具有改善的稳定性和出色的抗增殖特性的类似物。DLeu或DNle残基对PACE4的特异性也有所提高，而对被精氨酸模拟物修饰的肽（如4-ami基苄基酰胺）的特异性却降低了。
• 2H-PHTHALAZIN-1-ONE DERIVATIVES AND DRUGS COMPRISING THESE DERIVATIVES AS THE ACTIVE INGREDIENT
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP1148053A1

  公开（公告）日：2001-10-24

  Poly(ADP-ribose)polymerase inhibitors containing as the active ingredient 2H-phthalazin-1-one derivatives represented by general formula (I) (wherein each symbol is as defined in the description) or salts thereof. The compounds of the general formula (I) inhibit poly(ADP-ribose)polymerase and are useful as preventives and/or remedies for various ischemic diseases (brain, heart, digestive tract, skeletal muscle, retina, etc.), inflammatory diseases (inflammatory intestinal diseases, multiple encephalosclerosis, arthritis, etc.), nerve degeneration diseases (extrapyramidal disorder, Alzheimer's disease, muscular dystrophy, etc.), diabetes, shock, head trauma, renal insufficiency, hyperalgesia, etc. These compounds are also useful as sensitizers for agents against retroviruses (HIV, etc.) and chemotherapy for cancer.

  聚(ADP-核糖)聚合酶抑制剂，其活性成分为通式(I)代表的 2H-酞嗪-1-酮衍生物（其中各符号如描述中所定义）或其盐。 通式（I）化合物可抑制聚（ADP-核糖）聚合酶，可用于预防和/或治疗各种缺血性疾病（脑、心脏、消化道、骨骼肌、视网膜等）、炎症性疾病（炎症性心肌梗塞、心肌梗死、心律失常、心肌梗死等）。这些化合物可用于预防和/或治疗各种缺血性疾病（脑部、心脏、消化道、骨骼肌、视网膜等）、炎症性疾病（肠道炎症性疾病、多发性脑硬化症、关节炎等）、神经变性疾病（锥体外系障碍、老年痴呆症、肌肉萎缩症等）、糖尿病、休克、头部外伤、肾功能不全、痛觉减退等。这些化合物还可用作抗逆转录病毒（HIV 等）药物和癌症化疗的增敏剂。
• Synthesis of Biologically Important Guanidine-Containing Molecules Using Triflyl-Diurethane Protected Guanidines
  作者：Tracy J. Baker

  DOI：10.1055/s-1999-3653

  日期：1999.8
• Synthesis and Biological Evaluation of Guanidino Compounds Endowed with Subnanomolar Affinity as Competitive Inhibitors of Maize Polyamine Oxidase
  作者：Fabrizio Manetti、Alessandra Cona、Lucilla Angeli、Claudia Mugnaini、Francesco Raffi、Caterina Capone、Elena Dreassi、Alessandra Tania Zizzari、Alessandra Tisi、Rodolfo Federico、Maurizio Botta

  DOI：10.1021/jm900371z

  日期：2009.8.13

  Previous studies on agmatine and its derivatives suggested that the presence of hydrophobic groups on the guanidine moiety was a crucial key for inhibitory activity of maize polyamine oxidase. Accordingly, new lipophilic agmatine and iminoctadine derivatives were synthesized and tested for their ability to inhibit this enzyme. Several compounds showed an affinity in the nanomolar range, while a cyclopropylmethyl derivative of iminoctadine was found to be the most potent inhibitor of maize polyamine oxidase reported so far (K-i = 0.08 nM).
• Optimization of Furin Inhibitors To Protect against the Activation of Influenza Hemagglutinin H5 and Shiga Toxin
  作者：Hugo Gagnon、Sophie Beauchemin、Anna Kwiatkowska、Frédéric Couture、François D’Anjou、Christine Levesque、Frédérik Dufour、Adamy Roberge Desbiens、Rolland Vaillancourt、Sylvain Bernard、Roxane Desjardins、François Malouin、Yves L. Dory、Robert Day

  DOI：10.1021/jm400633d

  日期：2014.1.9

  Proprotein convertases (PCs) are crucial in the processing and entry of viral or bacterial protein precursors and confer increased infectivity of pathogens bearing a PC activation site, which results in increased symptom severity and lethality. Previously, we developed a nanomolar peptide inhibitor of PCs to prevent PC activation of infectious agents. Herein, we describe a peptidomimetic approach that increases the stability of this inhibitor for use in vivo to prevent systemic infections and cellular damage, such as that caused by influenza H5N1 and Shiga toxin. The addition of aza beta(3)-amino acids to both termini of the peptide successfully prevented influenza hemagglutinin 5 fusogenicity and Shiga toxin Vero toxicity in cell-based assays. The results from a cell-based model using stable shRNA-induced proprotein convertase knockdown indicate that only furin is the major proprotein convertase required for HAS cleavage.